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WO2006063069A3 - Conversion catalytique d'hydrofluoroalcanol en hydrofluoroalcene - Google Patents

Conversion catalytique d'hydrofluoroalcanol en hydrofluoroalcene Download PDF

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Publication number
WO2006063069A3
WO2006063069A3 PCT/US2005/044298 US2005044298W WO2006063069A3 WO 2006063069 A3 WO2006063069 A3 WO 2006063069A3 US 2005044298 W US2005044298 W US 2005044298W WO 2006063069 A3 WO2006063069 A3 WO 2006063069A3
Authority
WO
WIPO (PCT)
Prior art keywords
activity
r1234yf
selectivity
reaction
contact time
Prior art date
Application number
PCT/US2005/044298
Other languages
English (en)
Other versions
WO2006063069A2 (fr
Inventor
Sudip Mukhopadhyay
Haridasan K Nair
Hsuehsung Tung
Original Assignee
Honeywell Int Inc
Sudip Mukhopadhyay
Haridasan K Nair
Hsuehsung Tung
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Honeywell Int Inc, Sudip Mukhopadhyay, Haridasan K Nair, Hsuehsung Tung filed Critical Honeywell Int Inc
Priority to CN200580047980XA priority Critical patent/CN101115703B/zh
Priority to DE602005023650T priority patent/DE602005023650D1/de
Priority to EP05853260A priority patent/EP1828083B1/fr
Priority to AT05853260T priority patent/ATE481374T1/de
Priority to JP2007545599A priority patent/JP4958790B2/ja
Publication of WO2006063069A2 publication Critical patent/WO2006063069A2/fr
Publication of WO2006063069A3 publication Critical patent/WO2006063069A3/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C21/00—Acyclic unsaturated compounds containing halogen atoms
    • C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
    • C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne un procédé de conversion catalytique dans lequel du méthane est utilisé comme agent de déshydratation sélective pour la production de 2,3,3,3-tétrafluoro-1-propène (R1234yf) à partir de 2,2,3,3,3-pentafluoro-1-propanol. Ce procédé consiste à préparer et à utiliser des catalyseurs supportés à base de métaux de transition pour cette réaction, avec une activité élevée. Presque 58 % de la sélectivité par rapport au R1234yf est obtenue à un degré de conversion de l'alcool de 60 % à l'aide d'une maille de Ni non supportée comme catalyseur. Le Pd et le Pt présentent des degrés de conversion quasiment identiques. Toutefois, la sélectivité par rapport au produit désiré est faible. En fait, l'activité du catalyseur dépend du type de matériau de support, le charbon actif présentant une meilleure activité que l'alumine. Différents paramètres importants, tels que la température, la pression et le temps de contact, sont pris en compte pour optimiser le procédé. Une température et une pression élevées ont un effet néfaste sur le taux de formation du 1234yf. Cependant, le rendement le plus élevé par rapport au 1234yf est obtenu lorsque la réaction est réalisée à 494 °C, avec un temps de contact de 23 secondes.
PCT/US2005/044298 2004-12-09 2005-12-09 Conversion catalytique d'hydrofluoroalcanol en hydrofluoroalcene WO2006063069A2 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CN200580047980XA CN101115703B (zh) 2004-12-09 2005-12-09 氢氟链烷醇至氢氟烯烃的催化转化
DE602005023650T DE602005023650D1 (de) 2004-12-09 2005-12-09 Katalytische umwandlung von hydrofluoralkanol in hydrofluoralken
EP05853260A EP1828083B1 (fr) 2004-12-09 2005-12-09 Conversion catalytique d'hydrofluoroalcanol en hydrofluoroalcene
AT05853260T ATE481374T1 (de) 2004-12-09 2005-12-09 Katalytische umwandlung von hydrofluoralkanol in hydrofluoralken
JP2007545599A JP4958790B2 (ja) 2004-12-09 2005-12-09 ハイドロフルオロアルカノールのハイドロフルオロアルケンへの接触転化

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US11/006,922 US7026520B1 (en) 2004-12-09 2004-12-09 Catalytic conversion of hydrofluoroalkanol to hydrofluoroalkene
US11/006,922 2004-12-09

Publications (2)

Publication Number Publication Date
WO2006063069A2 WO2006063069A2 (fr) 2006-06-15
WO2006063069A3 true WO2006063069A3 (fr) 2006-08-17

Family

ID=36127701

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2005/044298 WO2006063069A2 (fr) 2004-12-09 2005-12-09 Conversion catalytique d'hydrofluoroalcanol en hydrofluoroalcene

Country Status (8)

Country Link
US (1) US7026520B1 (fr)
EP (1) EP1828083B1 (fr)
JP (1) JP4958790B2 (fr)
CN (1) CN101115703B (fr)
AT (1) ATE481374T1 (fr)
DE (1) DE602005023650D1 (fr)
ES (1) ES2351199T3 (fr)
WO (1) WO2006063069A2 (fr)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7880040B2 (en) * 2004-04-29 2011-02-01 Honeywell International Inc. Method for producing fluorinated organic compounds
US9308199B2 (en) * 2004-04-29 2016-04-12 Honeywell International Inc. Medicament formulations
US7674939B2 (en) * 2004-04-29 2010-03-09 Honeywell International Inc. Method for producing fluorinated organic compounds
JP4864879B2 (ja) * 2004-04-29 2012-02-01 ハネウェル・インターナショナル・インコーポレーテッド １，３，３，３−テトラフルオロプロペンの合成方法
US7951982B2 (en) * 2004-04-29 2011-05-31 Honeywell International Inc. Method for producing fluorinated organic compounds
US7659434B2 (en) * 2004-04-29 2010-02-09 Honeywell International Inc. Method for producing fluorinated organic compounds
US8383867B2 (en) 2004-04-29 2013-02-26 Honeywell International Inc. Method for producing fluorinated organic compounds
US7476771B2 (en) * 2005-11-01 2009-01-13 E.I. Du Pont De Nemours + Company Azeotrope compositions comprising 2,3,3,3-tetrafluoropropene and hydrogen fluoride and uses thereof
US7335804B2 (en) * 2005-11-03 2008-02-26 Honeywell International Inc. Direct conversion of HCFC 225ca/cb mixture
EP2066605B1 (fr) * 2006-09-05 2013-12-25 E.I. Du Pont De Nemours And Company Procédé de fabrication du 2,3,3,3-tétrafluoropropène
US7981312B2 (en) * 2006-10-31 2011-07-19 E. I. Du Pont De Nemours And Company Processes for producing and compositions comprising 2,3,3,3-tetrafluoropropene and/or 1,2,3,3-tetrafluoropropene
US9523026B2 (en) 2007-06-27 2016-12-20 Arkema Inc. Stabilized hydrochlorofluoroolefins and hydrofluoroolefins
KR101477485B1 (ko) * 2007-06-27 2014-12-30 알케마 인코포레이티드 안정화된 하이드로클로로플루오로올레핀과 하이드로플루오로올레핀
EP2215097A1 (fr) * 2007-11-20 2010-08-11 E. I. du Pont de Nemours and Company Synthèse d'hydrofluoroalcanols et d'hydrofluoroalcènes
US8058488B2 (en) * 2007-11-20 2011-11-15 E. I. Du Pont De Nemours And Company Synthesis of hydrofluoroalkanols and hydrofluoroalkenes
US8053612B2 (en) * 2008-05-30 2011-11-08 Honeywell International Inc. Process for dehydrochlorinating 1,1,1,2-tetrafluoro-2-chloropropane to 2,3,3,3-tetrafluoropropene in the presence of an alkali metal-doped magnesium oxyfluoride catalyst and methods for making the catalyst
KR101610009B1 (ko) * 2008-06-26 2016-04-07 알케마 인코포레이티드 1230ｘａ에서 1234ｙｆ로의 촉매식 기체상 불소화
WO2010087465A1 (fr) 2009-01-27 2010-08-05 Daikin Industries, Ltd. Procédé de préparation d'une oléfine contenant du fluor
RU2009149445A (ru) * 2009-12-29 2011-07-10 Е.И.Дюпон де Немур энд Компани (US) Синтез фторированных олефинов из фторированных спиртов
US8513474B2 (en) 2010-06-24 2013-08-20 Honeywell International Inc. Process for the manufacture of fluorinated olefins
CN102989489B (zh) 2011-09-14 2015-04-22 中化蓝天集团有限公司 一种制备2,3,3,3-四氟丙烯的方法
EP3023472B1 (fr) * 2014-09-25 2019-11-06 Daikin Industries, Ltd. Composition contenant un hfc et hfo
CN107382659B (zh) * 2017-08-08 2020-07-03 山东国邦药业有限公司 一种2,3,3,3-四氟丙烯的制备方法
US11209196B2 (en) * 2018-10-26 2021-12-28 The Chemours Company Fc, Llc HFO-1234ZE, HFO-1225ZC and HFO-1234YF compositions and processes for producing and using the compositions

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0328148A1 (fr) * 1988-02-12 1989-08-16 Daikin Industries, Limited Procédé de préparation d'oléfines fluorées

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2931840A (en) 1958-11-25 1960-04-05 Du Pont Process for preparing 2, 3, 3, 3-tetrafluoropropene
JP2755530B2 (ja) 1992-08-28 1998-05-20 株式会社トクヤマ 含フッ素アルコールの製造方法
JPH1129507A (ja) * 1997-07-11 1999-02-02 Asahi Glass Co Ltd ４−ポリフルオロアルキルブテンの製造方法

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0328148A1 (fr) * 1988-02-12 1989-08-16 Daikin Industries, Limited Procédé de préparation d'oléfines fluorées

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
BANKS R E ET AL: "Preparation of 2,3,3,3-tetrafluoropropene from trifluoroacetylacetone and sulphur tetrafluoride", JOURNAL OF FLUORINE CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 82, no. 2, May 1997 (1997-05-01), pages 171 - 174, XP004068447, ISSN: 0022-1139 *

Also Published As

Publication number Publication date
EP1828083B1 (fr) 2010-09-15
EP1828083A2 (fr) 2007-09-05
CN101115703B (zh) 2010-10-27
ATE481374T1 (de) 2010-10-15
JP2009518282A (ja) 2009-05-07
ES2351199T3 (es) 2011-02-01
DE602005023650D1 (de) 2010-10-28
WO2006063069A2 (fr) 2006-06-15
JP4958790B2 (ja) 2012-06-20
US7026520B1 (en) 2006-04-11
CN101115703A (zh) 2008-01-30

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